


If At First You Don't Succeed

by SupernaturallyObsessed



Series: Chuck Plays Matchmaker [3]
Category: Supernatural
Genre: Chuck Ships It, Fluff, Heart-to-Heart, Insecure Dean, M/M, Post-Episode: s11e23 Alpha and Omega
Language: English
Status: Completed
Published: 2017-01-15
Updated: 2017-01-15
Packaged: 2018-09-17 13:59:27
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,538
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9328010
Author URL: https://archiveofourown.org/users/SupernaturallyObsessed/pseuds/SupernaturallyObsessed
Summary: Chuck has been trying to get Castiel and Dean to admit their feelings for each other for ages with no success. He finally decides that a more direct approach is needed if the two are ever going to open up.(It’s not entirely necessary to read parts 1 and 2 first but they will give you some context.)





	

**Author's Note:**

> Hi guys! Sorry this took so long. I had a lot of trouble getting the story the way I wanted it. Hope you enjoy! If anyone is reading this who hasn’t read the previous stories, just know that this is canon divergent after 11.23 and skips the existence of Toni Bevell/British MoL.

Dean was in the garage cleaning the Impala when he sensed someone behind him. He turned around quickly, gun already out of his waistband and pointed at the intruder.

“Chuck?” he shouted in surprise. Dean was glad he had waited an extra second before pulling the trigger. Chuck was God so it wasn’t like a bullet would hurt him but the hunter had a feeling the response still wouldn’t have been a positive one. “I thought you were off sipping margaritas with Amara.” He slipped his gun back in his pants and picked up the rag he had dropped in his haste.

“Time works different where we are,” Chuck answered with a small shrug. “It’s only been three and a half weeks for you but it’s been longer for us.”

“Anything I can help you with?” Dean still felt a little awkward around Chuck but he was trying to act natural. He switched rags and grabbed the can of wax to finish off his cleaning job.

“There is actually. Can you take a break for a little while?”

“Uh, yeah. Sure.” He put his supplies back down and stood still, not sure what to do. Chuck snapped and suddenly they were both sitting on a quiet dock somewhere. “Why the change in scenery?”

“I just wanted to be able to talk without any distractions.”

“Oh. Okay.” The two men sat in an awkward silence for a few minutes before Chuck finally started talking again.

“How’s Castiel?”

“You brought me all the way to…wherever we are to ask about Cas?” Dean felt like he was missing something. “Couldn’t you just ask him yourself?”

“I could, but I wanted to talk to you.”

“He’s fine. Anything else I can do for you?” Chuck couldn’t hold back a laugh. It seemed Dean was as thick as ever. “Something funny?” the hunter asked.

“I’ve done it for you, you know,” Chuck said, as if that answered the question.

“Done what?”

“Brought him back. I’ve lost count of how many times I’ve saved him now. There were multiple times I was just going to let him die and move on to the peace he deserved but I couldn’t. He begged me to let him go back to you. I don’t think he knew I was listening but I could tell that he truly cared about you and that you felt the same. So I’ve continued bringing him back. And yet, when I came down here and started interacting directly with you all I found out that you two still haven’t admitted your feelings to each other.”

“Woah, woah, woah. What are you talking about? Cas is great and he’s family and all but I don’t have ‘feelings’ for him,” Dean said, a little too quickly to seem natural. It was clear he was trying to hide something.

“Why do you continue to deny yourself that which you desire the most?” Chuck asked. Dean opened his mouth to deny it once again but Chuck cut him off. “I’m God, remember? You can’t actually hide anything from me.” Dean paused and then let out a long sigh.

“Because he deserves way better than me, man. How could I ever dream of being good enough for an angel after everything I’ve done?”

“You’re incredibly worthy, Dean Winchester. I wouldn’t have continuously brought him back to life and tried to bring you together if you weren’t,” Chuck tried to explain. “Have you made mistakes? Yes, and some of them were very big mistakes, but Castiel has made mistakes as well. So have I for that matter.”

“I don’t know.” Dean could admit to himself that he did have feelings for the angel in question, but he wasn’t sure he could agree that he was worthy of said angel’s affections.

“Just talk to him. I won’t force you obviously but I will strongly request it.”

“And what if he turns me down?” That was probably Dean’s biggest fear if he was being honest with himself. Opening his heart like that was scary enough but the thought of being laughed at and rejected was worse.

“I don’t think he will.”

“But what if he does?” Dean pressed.

“Then you go back to how things were and I’ll leave the matter alone.” Dean was silent and Chuck had to force himself to not read the human’s thoughts. He truly wasn’t sure how Dean would respond.

“Okay,” the hunter finally said.

“Okay?”

“I’ll talk to him.” Chuck smiled.

“Sounds good. I’ll send you back to the bunker then.”

“Wait…” Dean didn’t get a chance to finish before Chuck snapped and the hunter found himself in one of the rooms in the bunker. He couldn’t immediately place which room it was though which was strange.

“Dean? How did you get in here?” a low voice behind him asked. Dean turned around slowly and found that he was in Castiel’s bedroom. The angel was sitting on his bed reading. He had removed his shoes, trench coat, and suit jacket and rolled his sleeves up to his elbows which was making it a little hard for Dean to focus.

“Uh, hey, Cas.” Dean had been telling the truth when he said he’d talk to Cas but he hadn’t meant to do it right that second. “I was talking to your dad actually and he kinda sent me here.” Cas gave his signature head tilt and squinted his eyes.

“My father was here?”

“Yeah. He showed up when I was working on the Impala and then took me to some lake somewhere to talk.” Castiel decided to focus on his curiosity rather than the fact that his father had gone out of his way to speak to Dean but hadn’t said a word to him.

“What did he want to speak to you about? And why did he then send you here instead of back with your car?”

“He actually wanted to talk about us,” Dean said. “Like you and me,” he clarified.

“Oh. Is everything alright?”

“Yeah, man. Everything’s fine.” Dean wasn’t really sure what to say at that point so he just ran a nervous hand down his face.

“Would you like to sit down, Dean?” Castiel asked after a moment of silence. The hunter nodded and sat gingerly on the edge of the bed. Castiel put down his book and moved so that he was sitting next to Dean. “It’s clear you have something on your mind, Dean. Talk to me.” Although the words came out as a statement, the tone was a soft one.

“Um…” How was he supposed to start? “You know you’re important to me, right?”

“Yes, Dean. You’ve said that you see me as a brother and that means a lot to me.”

“Right. But, uh, what if I cared about you as something other than a brother but was too scared to admit to it before?”

“Like what?” When the hunter hesitated the angel continued. “I care about you as well, Dean. You do not need to feel scared to tell me the truth.”

“Damnit, I’m not good at this whole emotion heart-to-heart stuff.” Dean looked down and saw that his hand and Castiel’s hand were pretty close to each other on the bed. Maybe he didn’t need to say it. With a deep breath for courage, Dean put his hand on top of Cas’ and gave it a light squeeze. When Cas turned his hand over and laced their fingers together Dean quickly looked up in surprise. “Cas?”

“Dean, I have cared about you since I first touched your soul in Hell,” Castiel said softly. “I did not understand my feelings right away but I do now. I have for a while.”

“Then why did you never say anything?”

“I couldn’t be sure that you felt the same way. I also did not wish to ever make you feel as if you were being pressured. More than anything else I want you to be happy, Dean. If you only wished for me to be your friend and brother then that was what I would be.”

“Oh,” Dean said, tilting his head to look once again at their joined hands.

“Yes, oh,” Castiel said with a small laugh.

“So, uh, what happens now?”

“What would you like to have happen? I have not been involved in a relationship before but I have a good understanding of the basic concepts from what I have seen in person and watched on tv.”

“I guess we should just take things slow,” Dean said. “I mean, we’ve known each other for a long time but we haven’t done any of this stuff yet. Plus you’ve never been in any relationship and I haven’t dated a guy before so we’re both in new territory.”

“Taking things slow sounds like a good idea,” Cas said with a smile. He gave Dean’s hand a reassuring squeeze. “How about we start with going out to dinner tonight?”

“I’d like that, Cas,” Dean answered, looking at Castiel again. He found that he was smiling as well. “Hey, can I try something?”

“What would that be?” Dean winked, leaned forward, and softly pressed his lips to Castiel’s. It was everything he could have imagined and more.

**Author's Note:**

> Thanks for reading! I really appreciate all of the support I’ve been getting. I’ve decided to mark this series as complete for now but I’m open to the possibility of continuing if you guys have suggestions of other stories you’d like to see or I get an unexpected idea.


End file.
